Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-21 23:41:26 UTC

Update Date

2021-10-01 16:54:24 UTC

HMDB ID

HMDB0301410

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA

Description

(2s,3r)-3-hydroxy-2-methylbutanoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (2S_3R)-3-hydroxy-2-methylbutanoic acid thioester of coenzyme A. (2s,3r)-3-hydroxy-2-methylbutanoyl-coa is an acyl-CoA with 4 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. (2s,3r)-3-hydroxy-2-methylbutanoyl-coa is therefore classified as a short chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. (2s,3r)-3-hydroxy-2-methylbutanoyl-coa, being a short chain acyl-CoA is a substrate for short chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA into (2S_3R)-3-Hydroxy-2-methylbutanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (2S_3R)-3-Hydroxy-2-methylbutanoylcarnitine is converted back to (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA occurs in four steps. First, since (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA is a short chain acyl-CoA it is the substrate for a short chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304102104412D          

 55 57  0  0  0  0            999 V2000
   14.1781   -7.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1781   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4637   -6.7082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7492   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0347   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3202   -7.1207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6058   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6058   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8913   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1768   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -7.1207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334   -7.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9065   -7.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315   -5.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -6.2957    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -7.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880   -5.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4611   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7466   -6.2957    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -7.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -5.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0321   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169   -7.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900   -7.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256   -8.4539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131   -9.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -9.7815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -9.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2725   -9.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -9.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8537   -8.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000   -8.1405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -8.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587  -10.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -6.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230   -6.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505   -6.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -5.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -5.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -5.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2610   -4.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -4.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8926   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8926   -5.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6071   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3215   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6071   -7.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 36 41  2  0  0  0  0
 33 41  1  0  0  0  0
 37 42  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 30 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 47 50  1  0  0  0  0
  2 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
M  END

HMDB0301410
     RDKit          3D
(2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   10.6628    2.4825    2.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4972    1.6226    2.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2950    2.2208    2.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5845    0.2345    2.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5607    0.2827    4.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8048   -0.4511    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8210   -0.3290    2.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9830   -1.4028    0.7838 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5179   -1.8671   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7315   -0.7471   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -1.3275   -1.4342 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6663   -0.4722   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8195    0.7706   -1.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -1.0363   -2.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.0954   -3.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -0.2778   -3.8276 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577   -1.2864   -3.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -1.8871   -2.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -1.5784   -4.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -0.6726   -5.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.7674   -3.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143   -2.9366   -2.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1281   -2.0503   -4.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.4784   -2.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.6170   -1.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    0.7379   -0.9707 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.9611    1.4271   -1.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    1.8629   -0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.3151    0.5730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8820    1.6011    1.4740 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8264    2.1548    2.4119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    2.8366    0.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    1.0170    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    0.0090    1.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9218   -0.5746    2.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7819    0.4572    2.8525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0427    0.1392    2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8354    1.2946    2.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0755    1.5106    2.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5314    2.6801    2.0524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5581    3.1752    1.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5465    4.3442    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6414    5.2434    0.5195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4266    4.6065   -0.1822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3935    3.7583   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3882    2.5970    0.5511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4920    2.3005    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.7472    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3210   -0.0453    0.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -1.5779    1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8651   -2.1082    0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.8052    0.7955 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0141   -4.4052    1.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5635   -4.2137    1.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8311   -4.4835   -0.7591 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5588    2.8041    3.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6294    3.4117    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6215    1.9776    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5739    1.5821    1.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    3.1670    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7018   -0.3691    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991    0.1689    4.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9925   -0.5798    4.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738    1.1990    4.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8287   -2.4946    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8168   -2.5964   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484   -0.2117   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2987   -0.0750    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924   -2.3456   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0138   -1.8336   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129   -1.4127   -3.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    0.9461   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4990   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523    0.2213   -4.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434   -2.5766   -4.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230    0.2436   -4.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310   -3.7993   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -3.2301   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -2.6860   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -2.7182   -3.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.1510   -4.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -2.6594   -5.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814   -0.2861   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    0.3428   -3.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    2.7933   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    3.5447    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1855    0.5100    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991   -0.7726    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -1.0921    3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5329   -0.4959    3.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6780    0.9081    3.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6074    6.0810   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4809    5.0739    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    3.9739   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6591   -1.3850    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8387   -0.3443   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1251   -2.3752    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -5.1199    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -5.4692   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 37 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  0
  3 60  1  0
  4 61  1  0
  5 62  1  0
  5 63  1  0
  5 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
 10 68  1  0
 11 69  1  0
 14 70  1  0
 14 71  1  0
 15 72  1  0
 15 73  1  0
 16 74  1  0
 19 75  1  0
 20 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 23 82  1  0
 24 83  1  0
 24 84  1  0
 28 85  1  0
 32 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 37 90  1  0
 39 91  1  0
 43 92  1  0
 43 93  1  0
 45 94  1  0
 48 95  1  0
 49 96  1  0
 50 97  1  0
 54 98  1  0
 55 99  1  0
M  END


  Mrv1652304102104412D          

 55 57  0  0  0  0            999 V2000
   14.1781   -7.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1781   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4637   -6.7082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7492   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0347   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3202   -7.1207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6058   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6058   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8913   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1768   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4624   -7.1207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7479   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334   -7.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9065   -7.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315   -5.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -6.2957    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -7.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880   -5.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4611   -5.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7466   -6.2957    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591   -7.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -5.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0321   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5169   -7.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900   -7.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256   -8.4539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131   -9.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -9.7815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -9.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2725   -9.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -9.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8537   -8.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000   -8.1405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326   -8.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587  -10.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -6.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230   -6.8995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505   -6.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -5.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -5.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -5.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2610   -4.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -4.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8926   -6.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8926   -5.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6071   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3215   -6.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6071   -7.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 36 41  2  0  0  0  0
 33 41  1  0  0  0  0
 37 42  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 30 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 47 50  1  0  0  0  0
  2 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301410

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)

> <INCHI_KEY>
PEKYNTFSOBAABV-UHFFFAOYSA-N

> <FORMULA>
C26H44N7O18P3S

> <MOLECULAR_WEIGHT>
867.65

> <EXACT_MASS>
867.167639773

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
78.95372540890766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-5.502293119814627

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.820978781339821

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.86

> <JCHEM_REFRACTIVITY>
187.60290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301410
     RDKit          3D
(2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   10.6628    2.4825    2.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4972    1.6226    2.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2950    2.2208    2.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5845    0.2345    2.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5607    0.2827    4.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8048   -0.4511    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8210   -0.3290    2.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9830   -1.4028    0.7838 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5179   -1.8671   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7315   -0.7471   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -1.3275   -1.4342 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6663   -0.4722   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8195    0.7706   -1.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -1.0363   -2.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.0954   -3.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -0.2778   -3.8276 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577   -1.2864   -3.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -1.8871   -2.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -1.5784   -4.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -0.6726   -5.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.7674   -3.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143   -2.9366   -2.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1281   -2.0503   -4.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.4784   -2.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.6170   -1.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    0.7379   -0.9707 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.9611    1.4271   -1.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    1.8629   -0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.3151    0.5730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8820    1.6011    1.4740 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8264    2.1548    2.4119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    2.8366    0.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    1.0170    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    0.0090    1.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9218   -0.5746    2.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7819    0.4572    2.8525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0427    0.1392    2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8354    1.2946    2.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0755    1.5106    2.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5314    2.6801    2.0524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5581    3.1752    1.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5465    4.3442    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6414    5.2434    0.5195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4266    4.6065   -0.1822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3935    3.7583   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3882    2.5970    0.5511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4920    2.3005    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.7472    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3210   -0.0453    0.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -1.5779    1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8651   -2.1082    0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.8052    0.7955 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0141   -4.4052    1.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5635   -4.2137    1.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8311   -4.4835   -0.7591 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5588    2.8041    3.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6294    3.4117    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6215    1.9776    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5739    1.5821    1.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    3.1670    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7018   -0.3691    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991    0.1689    4.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9925   -0.5798    4.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738    1.1990    4.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8287   -2.4946    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8168   -2.5964   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484   -0.2117   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2987   -0.0750    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924   -2.3456   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0138   -1.8336   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129   -1.4127   -3.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    0.9461   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4990   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523    0.2213   -4.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434   -2.5766   -4.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230    0.2436   -4.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310   -3.7993   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -3.2301   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -2.6860   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -2.7182   -3.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.1510   -4.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -2.6594   -5.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814   -0.2861   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    0.3428   -3.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    2.7933   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    3.5447    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1855    0.5100    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991   -0.7726    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -1.0921    3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5329   -0.4959    3.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6780    0.9081    3.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6074    6.0810   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4809    5.0739    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    3.9739   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6591   -1.3850    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8387   -0.3443   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1251   -2.3752    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -5.1199    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -5.4692   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 37 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  0
  3 60  1  0
  4 61  1  0
  5 62  1  0
  5 63  1  0
  5 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
 10 68  1  0
 11 69  1  0
 14 70  1  0
 14 71  1  0
 15 72  1  0
 15 73  1  0
 16 74  1  0
 19 75  1  0
 20 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 23 82  1  0
 24 83  1  0
 24 84  1  0
 28 85  1  0
 32 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 37 90  1  0
 39 91  1  0
 43 92  1  0
 43 93  1  0
 45 94  1  0
 48 95  1  0
 49 96  1  0
 50 97  1  0
 54 98  1  0
 55 99  1  0
M  END

HEADER    PROTEIN                                 10-APR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-APR-21         0                                  
HETATM    1  O   UNK     0      26.466 -14.832   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      26.466 -13.292   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      25.132 -12.522   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      23.798 -13.292   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.465 -12.522   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      21.131 -13.292   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      19.797 -12.522   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.797 -10.982   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.464 -13.292   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.130 -12.522   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      15.796 -13.292   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.463 -12.522   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.463 -10.982   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.129 -13.292   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.129 -14.832   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.795 -12.522   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.025 -13.856   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.565 -11.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.462 -11.752   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.128 -12.522   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       7.794 -11.752   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0       7.024 -13.086   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.564 -10.418   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.461 -10.982   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0       5.127 -11.752   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0       5.897 -13.086   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.357 -10.418   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.793 -12.522   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.460 -11.752   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.126 -12.522   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.965 -14.054   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.541 -14.374   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -1.168 -15.781   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      -0.398 -17.114   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -1.428 -18.259   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -2.835 -17.632   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.242 -18.259   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -5.488 -17.354   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -5.327 -15.822   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -3.920 -15.196   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      -2.674 -16.101   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      -4.403 -19.790   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      -1.311 -13.040   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.843 -12.879   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.281 -11.896   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.601 -10.389   0.000  0.00  0.00           O+0
HETATM   47  P   UNK     0       0.543  -9.359   0.000  0.00  0.00           P+0
HETATM   48  O   UNK     0       1.574 -10.503   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -0.487  -8.214   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       1.688  -8.328   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      27.800 -12.522   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      27.800 -10.982   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      29.133 -13.292   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      30.467 -12.522   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      29.133 -14.832   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   45                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   43                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   33                                                  
CONECT   42   37                                                            
CONECT   43   32   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   30   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47                                                            
CONECT   51    2   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

COMPND    HMDB0301410
HETATM    1  C1  UNL     1      10.663   2.482   2.569  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.497   1.623   2.096  1.00  0.00           C  
HETATM    3  O1  UNL     1       8.295   2.221   2.451  1.00  0.00           O  
HETATM    4  C3  UNL     1       9.585   0.235   2.709  1.00  0.00           C  
HETATM    5  C4  UNL     1       9.561   0.283   4.205  1.00  0.00           C  
HETATM    6  C5  UNL     1      10.805  -0.451   2.238  1.00  0.00           C  
HETATM    7  O2  UNL     1      11.821  -0.329   2.974  1.00  0.00           O  
HETATM    8  S1  UNL     1      10.983  -1.403   0.784  1.00  0.00           S  
HETATM    9  C6  UNL     1       9.518  -1.867  -0.095  1.00  0.00           C  
HETATM   10  C7  UNL     1       8.732  -0.747  -0.707  1.00  0.00           C  
HETATM   11  N1  UNL     1       7.599  -1.328  -1.434  1.00  0.00           N  
HETATM   12  C8  UNL     1       6.666  -0.472  -2.056  1.00  0.00           C  
HETATM   13  O3  UNL     1       6.819   0.771  -1.966  1.00  0.00           O  
HETATM   14  C9  UNL     1       5.488  -1.036  -2.823  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.516   0.095  -3.096  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.355  -0.278  -3.828  1.00  0.00           N  
HETATM   17  C11 UNL     1       2.458  -1.286  -3.383  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.697  -1.887  -2.314  1.00  0.00           O  
HETATM   19  C12 UNL     1       1.266  -1.578  -4.226  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.130  -0.673  -5.249  1.00  0.00           O  
HETATM   21  C13 UNL     1       0.005  -1.767  -3.433  1.00  0.00           C  
HETATM   22  C14 UNL     1       0.114  -2.937  -2.468  1.00  0.00           C  
HETATM   23  C15 UNL     1      -1.128  -2.050  -4.376  1.00  0.00           C  
HETATM   24  C16 UNL     1      -0.253  -0.478  -2.649  1.00  0.00           C  
HETATM   25  O6  UNL     1      -1.421  -0.617  -1.890  1.00  0.00           O  
HETATM   26  P1  UNL     1      -1.786   0.738  -0.971  1.00  0.00           P  
HETATM   27  O7  UNL     1      -2.961   1.427  -1.673  1.00  0.00           O  
HETATM   28  O8  UNL     1      -0.548   1.863  -0.902  1.00  0.00           O  
HETATM   29  O9  UNL     1      -2.331   0.315   0.573  1.00  0.00           O  
HETATM   30  P2  UNL     1      -2.882   1.601   1.474  1.00  0.00           P  
HETATM   31  O10 UNL     1      -1.826   2.155   2.412  1.00  0.00           O  
HETATM   32  O11 UNL     1      -3.566   2.837   0.535  1.00  0.00           O  
HETATM   33  O12 UNL     1      -4.131   1.017   2.479  1.00  0.00           O  
HETATM   34  C17 UNL     1      -4.777   0.009   1.755  1.00  0.00           C  
HETATM   35  C18 UNL     1      -5.922  -0.575   2.588  1.00  0.00           C  
HETATM   36  O13 UNL     1      -6.782   0.457   2.853  1.00  0.00           O  
HETATM   37  C19 UNL     1      -8.043   0.139   2.398  1.00  0.00           C  
HETATM   38  N3  UNL     1      -8.835   1.295   2.074  1.00  0.00           N  
HETATM   39  C20 UNL     1     -10.076   1.511   2.552  1.00  0.00           C  
HETATM   40  N4  UNL     1     -10.531   2.680   2.052  1.00  0.00           N  
HETATM   41  C21 UNL     1      -9.558   3.175   1.264  1.00  0.00           C  
HETATM   42  C22 UNL     1      -9.547   4.344   0.534  1.00  0.00           C  
HETATM   43  N5  UNL     1     -10.641   5.243   0.520  1.00  0.00           N  
HETATM   44  N6  UNL     1      -8.427   4.607  -0.182  1.00  0.00           N  
HETATM   45  C23 UNL     1      -7.394   3.758  -0.167  1.00  0.00           C  
HETATM   46  N7  UNL     1      -7.388   2.597   0.551  1.00  0.00           N  
HETATM   47  C24 UNL     1      -8.492   2.301   1.280  1.00  0.00           C  
HETATM   48  C25 UNL     1      -7.791  -0.747   1.197  1.00  0.00           C  
HETATM   49  O14 UNL     1      -7.321  -0.045   0.100  1.00  0.00           O  
HETATM   50  C26 UNL     1      -6.631  -1.578   1.736  1.00  0.00           C  
HETATM   51  O15 UNL     1      -5.865  -2.108   0.717  1.00  0.00           O  
HETATM   52  P3  UNL     1      -6.006  -3.805   0.795  1.00  0.00           P  
HETATM   53  O16 UNL     1      -5.014  -4.405   1.761  1.00  0.00           O  
HETATM   54  O17 UNL     1      -7.564  -4.214   1.331  1.00  0.00           O  
HETATM   55  O18 UNL     1      -5.831  -4.483  -0.759  1.00  0.00           O  
HETATM   56  H1  UNL     1      10.559   2.804   3.616  1.00  0.00           H  
HETATM   57  H2  UNL     1      10.629   3.412   1.958  1.00  0.00           H  
HETATM   58  H3  UNL     1      11.622   1.978   2.378  1.00  0.00           H  
HETATM   59  H4  UNL     1       9.574   1.582   1.010  1.00  0.00           H  
HETATM   60  H5  UNL     1       8.302   3.167   2.169  1.00  0.00           H  
HETATM   61  H6  UNL     1       8.702  -0.369   2.373  1.00  0.00           H  
HETATM   62  H7  UNL     1      10.599   0.169   4.629  1.00  0.00           H  
HETATM   63  H8  UNL     1       8.992  -0.580   4.587  1.00  0.00           H  
HETATM   64  H9  UNL     1       9.074   1.199   4.606  1.00  0.00           H  
HETATM   65  H10 UNL     1       8.829  -2.495   0.559  1.00  0.00           H  
HETATM   66  H11 UNL     1       9.817  -2.596  -0.897  1.00  0.00           H  
HETATM   67  H12 UNL     1       9.348  -0.212  -1.454  1.00  0.00           H  
HETATM   68  H13 UNL     1       8.299  -0.075   0.068  1.00  0.00           H  
HETATM   69  H14 UNL     1       7.492  -2.346  -1.488  1.00  0.00           H  
HETATM   70  H15 UNL     1       5.014  -1.834  -2.224  1.00  0.00           H  
HETATM   71  H16 UNL     1       5.913  -1.413  -3.770  1.00  0.00           H  
HETATM   72  H17 UNL     1       5.027   0.946  -3.599  1.00  0.00           H  
HETATM   73  H18 UNL     1       4.237   0.499  -2.085  1.00  0.00           H  
HETATM   74  H19 UNL     1       3.152   0.221  -4.745  1.00  0.00           H  
HETATM   75  H20 UNL     1       1.443  -2.577  -4.732  1.00  0.00           H  
HETATM   76  H21 UNL     1       1.023   0.244  -4.897  1.00  0.00           H  
HETATM   77  H22 UNL     1       0.631  -3.799  -2.931  1.00  0.00           H  
HETATM   78  H23 UNL     1      -0.934  -3.230  -2.237  1.00  0.00           H  
HETATM   79  H24 UNL     1       0.655  -2.686  -1.540  1.00  0.00           H  
HETATM   80  H25 UNL     1      -1.876  -2.718  -3.875  1.00  0.00           H  
HETATM   81  H26 UNL     1      -1.611  -1.151  -4.796  1.00  0.00           H  
HETATM   82  H27 UNL     1      -0.704  -2.659  -5.222  1.00  0.00           H  
HETATM   83  H28 UNL     1       0.581  -0.286  -1.949  1.00  0.00           H  
HETATM   84  H29 UNL     1      -0.309   0.343  -3.366  1.00  0.00           H  
HETATM   85  H30 UNL     1      -0.822   2.793  -1.026  1.00  0.00           H  
HETATM   86  H31 UNL     1      -3.846   3.545   1.185  1.00  0.00           H  
HETATM   87  H32 UNL     1      -5.185   0.510   0.854  1.00  0.00           H  
HETATM   88  H33 UNL     1      -4.099  -0.773   1.394  1.00  0.00           H  
HETATM   89  H34 UNL     1      -5.516  -1.092   3.465  1.00  0.00           H  
HETATM   90  H35 UNL     1      -8.533  -0.496   3.159  1.00  0.00           H  
HETATM   91  H36 UNL     1     -10.678   0.908   3.224  1.00  0.00           H  
HETATM   92  H37 UNL     1     -10.607   6.081  -0.076  1.00  0.00           H  
HETATM   93  H38 UNL     1     -11.481   5.074   1.099  1.00  0.00           H  
HETATM   94  H39 UNL     1      -6.512   3.974  -0.737  1.00  0.00           H  
HETATM   95  H40 UNL     1      -8.659  -1.385   0.933  1.00  0.00           H  
HETATM   96  H41 UNL     1      -7.839  -0.344  -0.690  1.00  0.00           H  
HETATM   97  H42 UNL     1      -7.125  -2.375   2.366  1.00  0.00           H  
HETATM   98  H43 UNL     1      -7.576  -5.120   1.747  1.00  0.00           H  
HETATM   99  H44 UNL     1      -5.906  -5.469  -0.622  1.00  0.00           H  
CONECT    1    2   56   57   58
CONECT    2    3    4   59
CONECT    3   60
CONECT    4    5    6   61
CONECT    5   62   63   64
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   65   66
CONECT   10   11   67   68
CONECT   11   12   69
CONECT   12   13   13   14
CONECT   14   15   70   71
CONECT   15   16   72   73
CONECT   16   17   74
CONECT   17   18   18   19
CONECT   19   20   21   75
CONECT   20   76
CONECT   21   22   23   24
CONECT   22   77   78   79
CONECT   23   80   81   82
CONECT   24   25   83   84
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   85
CONECT   29   30
CONECT   30   31   31   32   33
CONECT   32   86
CONECT   33   34
CONECT   34   35   87   88
CONECT   35   36   50   89
CONECT   36   37
CONECT   37   38   48   90
CONECT   38   39   47
CONECT   39   40   40   91
CONECT   40   41
CONECT   41   42   42   47
CONECT   42   43   44
CONECT   43   92   93
CONECT   44   45   45
CONECT   45   46   94
CONECT   46   47   47
CONECT   48   49   50   95
CONECT   49   96
CONECT   50   51   97
CONECT   51   52
CONECT   52   53   53   54   55
CONECT   54   98
CONECT   55   99
END

HMDB0301410
     RDKit          3D
(2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   10.6628    2.4825    2.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4972    1.6226    2.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2950    2.2208    2.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5845    0.2345    2.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5607    0.2827    4.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8048   -0.4511    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8210   -0.3290    2.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9830   -1.4028    0.7838 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5179   -1.8671   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7315   -0.7471   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5988   -1.3275   -1.4342 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6663   -0.4722   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8195    0.7706   -1.9660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881   -1.0363   -2.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.0954   -3.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -0.2778   -3.8276 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4577   -1.2864   -3.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -1.8871   -2.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -1.5784   -4.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -0.6726   -5.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.7674   -3.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143   -2.9366   -2.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1281   -2.0503   -4.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.4784   -2.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.6170   -1.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    0.7379   -0.9707 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.9611    1.4271   -1.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    1.8629   -0.9016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.3151    0.5730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8820    1.6011    1.4740 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8264    2.1548    2.4119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    2.8366    0.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1313    1.0170    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    0.0090    1.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9218   -0.5746    2.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7819    0.4572    2.8525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0427    0.1392    2.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8354    1.2946    2.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0755    1.5106    2.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5314    2.6801    2.0524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5581    3.1752    1.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5465    4.3442    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6414    5.2434    0.5195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4266    4.6065   -0.1822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3935    3.7583   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3882    2.5970    0.5511 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4920    2.3005    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.7472    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3210   -0.0453    0.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -1.5779    1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8651   -2.1082    0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.8052    0.7955 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.0141   -4.4052    1.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5635   -4.2137    1.3306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8311   -4.4835   -0.7591 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5588    2.8041    3.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6294    3.4117    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6215    1.9776    2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5739    1.5821    1.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    3.1670    2.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7018   -0.3691    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991    0.1689    4.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9925   -0.5798    4.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0738    1.1990    4.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8287   -2.4946    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8168   -2.5964   -0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484   -0.2117   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2987   -0.0750    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924   -2.3456   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0138   -1.8336   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9129   -1.4127   -3.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    0.9461   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4990   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523    0.2213   -4.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434   -2.5766   -4.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230    0.2436   -4.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310   -3.7993   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -3.2301   -2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554   -2.6860   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -2.7182   -3.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.1510   -4.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7036   -2.6594   -5.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814   -0.2861   -1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085    0.3428   -3.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    2.7933   -1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    3.5447    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1855    0.5100    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991   -0.7726    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5160   -1.0921    3.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5329   -0.4959    3.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6780    0.9081    3.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6074    6.0810   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4809    5.0739    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    3.9739   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6591   -1.3850    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8387   -0.3443   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1251   -2.3752    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5756   -5.1199    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9063   -5.4692   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 37 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  0
  3 60  1  0
  4 61  1  0
  5 62  1  0
  5 63  1  0
  5 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
 10 68  1  0
 11 69  1  0
 14 70  1  0
 14 71  1  0
 15 72  1  0
 15 73  1  0
 16 74  1  0
 19 75  1  0
 20 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 23 82  1  0
 24 83  1  0
 24 84  1  0
 28 85  1  0
 32 86  1  0
 34 87  1  0
 34 88  1  0
 35 89  1  0
 37 90  1  0
 39 91  1  0
 43 92  1  0
 43 93  1  0
 45 94  1  0
 48 95  1  0
 49 96  1  0
 50 97  1  0
 54 98  1  0
 55 99  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-hydroxy-2-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidate	Generator
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-hydroxy-2-methylbutanoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidate	Generator
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-hydroxy-2-methylbutanoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid	Generator

Chemical Formula

C₂₆H₄₄N₇O₁₈P₃S

Average Molecular Weight

867.65

Monoisotopic Molecular Weight

867.167639773

IUPAC Name

{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)

InChI Key

PEKYNTFSOBAABV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-hydroxyacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.48	ALOGPS
logP	-5.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	187.6 m³·mol⁻¹	ChemAxon
Polarizability	78.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	260.855	32859911
AllCCS	[M+H-H2O]+	261.325	32859911
AllCCS	[M+Na]+	260.22	32859911
AllCCS	[M+NH4]+	260.369	32859911
AllCCS	[M-H]-	257.803	32859911
AllCCS	[M+Na-2H]-	262.147	32859911
AllCCS	[M+HCOO]-	266.959	32859911
DeepCCS	[M+H]+	217.824	30932474
DeepCCS	[M-H]-	215.999	30932474
DeepCCS	[M-2H]-	249.539	30932474
DeepCCS	[M+Na]+	224.669	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 10V, Positive-QTOF	splash10-014i-0000000190-c7660cb8074cdb7785f2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 20V, Positive-QTOF	splash10-000i-1900002440-0c30d5ed7ad3fc1eb9fc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 40V, Positive-QTOF	splash10-03di-0039000000-7e8f0bc2c371968532d8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 10V, Negative-QTOF	splash10-014i-0000000090-f99797af7605477f8118	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 20V, Negative-QTOF	splash10-00li-9200001110-c3ad6043a456b94e2991	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA 40V, Negative-QTOF	splash10-004r-6103703920-89a34df340ee562cb16f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Abe T, Fujino T, Fukuyama R, Minoshima S, Shimizu N, Toh H, Suzuki H, Yamamoto T: Human long-chain acyl-CoA synthetase: structure and chromosomal location. J Biochem. 1992 Jan;111(1):123-8. [PubMed:1607358 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for (2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA (HMDB0301410)

MOL for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

3D MOL for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

3D SDF for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

3D-SDF for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

PDB for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

3D PDB for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

SMILES for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

INCHI for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

Structure for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

3D Structure for HMDB0301410 ((2S,3R)-3-Hydroxy-2-methylbutanoyl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra